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Title: | Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates | Authors: | Soares, Maria I. L. Gomes, Clara S. B. Oliveira, M. Conceição Marçalo, Joaquim Pinho e Melo, Teresa M. V. D. |
Issue Date: | 18-Nov-2021 | Publisher: | Royal Society of Chemistry | Project: | The authors thank Coimbra Chemistry Centre (CQC), supported by the Portuguese Agency for Scientific Research “Fundação para a Ciência e a Tecnologia” (FCT), through project UIDB/00313/2020 and UIDP/00313/2020, co-funded by COMPETE2020-UE. The Associate Laboratory for Green Chemistry – LAQV, the Applied Molecular Biosciences Unit – UCIBIO and the Associate Laboratory i4HB – Institute for Health and Bioeconomy, are financed by national funds from FCT/MCTES (UIDB/50006/2020, UIDP/50006/2020, UIDB/ 04378/2020, UIDP/04378/2020, LA/P/0140/2020, respectively). Single-crystal X-ray infrastructure financed by FCT-MCTES through project RECI/BBB-BEP/0124/2012. The authors also acknowledge the UC-NMR facility for obtaining the NMR data (http://www.nmrccc.uc.pt). This work was also supported by FCT through project UIDB/00100/2020 (CQE) and through RNEM – Portuguese Mass Spectrometry Network, ref. LISBOA-01-0145-FEDER-022125, also supported by the Lisboa Regional Operational Programme (Lisboa2020), under the PT2020 Partnership Agreement, via the European Regional Development Fund (ERDF). | Serial title, monograph or event: | Organic & Biomolecular Chemistry | Volume: | 19 | Issue: | 44 | Abstract: | The DABCO-catalyzed [3 + 3] annulation between 3-nitro-2H-chromenes and benzyl 2,3-butadienoate has been developed as a route to 5H-chromeno[3,4-b]pyridine derivatives. Under optimal reaction conditions, 5H-chromeno[3,4-b]pyridines incorporating two allenoate units were obtained in moderate to good yields (30-76%). The same type of transformation could be carried out using butynoates as allene surrogates. Mechanistic studies by mass spectrometry allowed the identification of the key intermediates involved in the reaction mechanism. The reported synthetic methodology represents an entirely new approach for the synthesis of the 5H-chromeno[3,4-b]pyridine core structure based on allene chemistry. | URI: | https://hdl.handle.net/10316/107453 | DOI: | 10.1039/d1ob01130h | Rights: | embargoedAccess |
Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
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Soares2021OrgBiomolChem.pdf | 978.44 kB | Adobe PDF | View/Open |
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